Figuring out the names of Caribbean islands was as daunting as learning island groups of the South Pacific. First, there’s a whole lot of them! And then, where does one country end and the next begin? And could I please have a Venn diagram that shows regions and island groups and countries? At least most Caribbean place names have intuitive pronunciation for English speakers (first guesses at cruiser destinations like Kiribati, Papeete, Whangarei, Nadi, Pago Pago, etc. are usually not correct). Cruiser cred points for anyone who can correctly spell these phonetically in the comments!

Quick geography tangent: Antilles is a general term that refers to ALL Caribbean islands, based on the legend of a phantom island—Antillia—that a 15th century Italian-born historian placed in the Atlantic, far to the west from Europe. As boats sailed from Europe to the Americas and the region became better mapped, Antillia gradually disappeared but the general reference for islands to the far west remained.

“Antilles” is less frequently heard than the subset as they are divided into—Greater and Lesser—which are conveniently grouped geographically: Greater Antilles being larger islands to the north (Cuba, Hispaniola, Puerto Rico, Jamaica), and Lesser Antilles being the smaller balance scattered to the east and south. The Lesser Antilles are further divided into windward and leeward islands, which include French Antilles and Dutch Antilles, and then there’s the Lucayan archipelago, didja know the ABCs are an island group not just an alphabet, and… right, too easy to get confused!

Most of our travel through the Greater Antilles was a tease of changing plans as we sought safer waters for hurricane season. We may regret postponing a visit to Cuba, as it is increasingly difficult for a US-flagged boat to access. Passing over Hispaniola I truly regret, and acknowledge the crew of Uma for their generous, speedy, thoughtful, and realistic guidance for visiting Haiti. Where armchair sailors who have no Haitian experience pronounced our certain death if we visited, Kika was a voice of reason: sharing contacts from their months in Haiti, annotating maps, suggesting anchorages. Anchorages we looked forward to visiting, until an unexpected weather window for quicker easting opened. And with that window, we skipped across both Haiti and the Dominican Republic (which together comprise Hispaniola) with one lone (but very memorable) stop. Puerto Rico would be similarly abbreviated if it hadn’t been for the matter of urgent health care. When we moved east again, expected to fast track the remaining necessary stops until Grenada. Anyone who knows our speed is laughing right now…we don’t “fast track” anything very well!

Expecting to skip through Puerto Rico’s eastern island of Culebra as just a pit stop, weather dictated otherwise. With the excellent hurricane hole in Salinas a day sail behind it was worth watching to see what the latest wave from Africa would do.

At left, the “spaghetti model” for the low which eventually became hurricane Gert; at right, the NOAA outlook about a week and a half later

Weather system 99L eventually became hurricane Gert, happily stayed away, but the active picture illustrates reasons behind the frequent pauses…also known as the wonderful opportunity to spend time with people previously known through the interwebs. Sophie and family, who our kids played endless rounds of jump-off-the-bow-swim-back-climb-aboard-repeat.

Long awaited was meeting with Sue and Rick of Orion. Sue and I have been corresponding for quite a few years. You can see the solemnity of the occasion when we finally met up.

Anchored more than a week next to Orion in the Dakity bay corner of Ensenada Honda, they shared “their” Culebra. Long time Puerto Rico residents, they know this area intimately and it was a privilege to experience it with their guidance—from visiting a small museum to exploring on the island.

Sunset behind Totem…

…sunrise in front of Orion.

Walking in Culebra with Sue & Rick

Coaching clients taking a few weeks on their Dean 44 catamaran joined in. This turned into several fun nights of sundowners (and beyond: would that be moonrisers?), playing at the beautiful little island of Culebrita, and some of the best tacos I’ve had in years. For all those memories, somehow I only ended up with pictures of the tacos… and a cucumber-jalapeno margarita, which was even better than you think. Mimzy crew, that was a lot of fun – we’d like a repeat in the South Pacific!

pork belly, beef tongue, and a truly spicy margarita

After a schedule centered around doctors’ appointments it was nice to fall back into a more normal family routine. Setting up dinner in the solar oven. Cribbage in the cockpit when the afternoon cools off. Jamie and I were on swimming restriction while our stitches healed, but the kids weren’t, and drawing them to the reef for a closer peek was Miss Dakity. That’s the name Sue gave a young flamingo that blew into Culebra earlier in the year and seems to have set up (solo) shop. Fuzzy pic… attempting with a zoom lens from simply way too far away, from a moving platform!

The unplanned month in Puerto Rico was more pleasant than anticipated, medical stuff notwithstanding. More than that, it zoomed PR way up on the list of “places we could see living someday.” There is a vibe that I’m not sure how to describe: maybe it’s why year after year, Puerto Ricans are listed on a long-term study by the University of Michigan as among the happiest people in the world. There is a friendliness here that’s well over the bar of most. The gregariousness of “Puerto Rican Navy” (affectionate name for weekend powerboaters) dancing on the beach in Culebrita (and leaving no sign of their presence behind). The warmth and care and HOUSECALL by Dr Villa. The smile that greeted meager Spanish, helpful instead of patronizing. Even if it weren’t for the beautiful landscape and history to soak in, we’d be sold.

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Behan Gifford

Behan Gifford graduated from sailing a Sunfish on Lake Huron to racing dinghies at college in Connecticut. Her second date with a cute sailmaker took her on an offshore race aboard a J/35; she threw up, but he married her anyway (she aimed to leeward). A move to Puget Sound resulted in a switch from racing for cruising, and in 2008, she began a nomadic journey on a Stevens 47, Totem. Behan, Jamie, and their three children have since crossed the Pacific, Indian, and Atlantic oceans and are currently cruising between the USA and Caribbean. Follow the Totem family here on SAILfeed and at SailingTotem.com